Pharmaceutical compounds.



ncense.

MAX ENGELMANN, OF ELBERFELD, FRIEDB. BAYER &, CO., OF ELBERFELD, GE

Y, ASSIGNOR T0 FARBENFABRIKEN VOBM. RMANY, A CORPORATION OF GERMANY.

?HARMACEUTICAL COMPOUNDS.

No Drawing.

TocZZ whom it may concern Be it known that 1, MAX ENGELMANN, doctor of philosophy, chemist, citizen of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in Pharmaceutical Compounds, of which the following is a specification.

My application Serial No. 5345325 relates to the preparation of easily soluble compounds derived from the ort-ho-oXy-mercuric compound of salicylic acid anhydrid (hydrargyrum salieylieum) which are prepared from the knownortho-oXy-mercuric salicylic acid anhydrid (hydrargyrum salieylicum of the German Pharmacopoeia) by treating it with alkali and an amino acid or with the alkali salts of an amino acid;v The same products result by at first treatin the above mentioned anhydrids with alkalis" and then treating the products thus obtained with amino fatty acids. I have now found that in this process other oxymercuricl carboxylic acid compounds, especially oxymercuric carboxylic acids and their anhydrids can be used instead of the salicylate of mercuric oxid c. g. the oxymercuric benzoic acid anhydrid (see Bc richte dew Dcutschcn Ghcmz'sclzen Gesellschaft 35, p. 2870) The new compounds thus obtained probably possess the following graphically represented constitution:

co.on

in which M stands for metal, X for an amino Example 2: 320 parts of the oxymercuric meta-oxybenzoic acid anhydrid (the same as described in Example 1) are added to a solution of 131 parts of asparagin in 1000 parts of normal NaOH. The solution is filtered and the filtrate is evaporated. The new compound separates in crystals. The whitish product is easily soluble in water, insoluble in alcohol, ether and benzene, and is Specification of Letters Patent.

Patented Apr. 2Q, 1013.

Application filed. October 4, 1910. Serial No. 585,304.

fatty acid and R for an aromatic nucleus,- are whitish odorless compounds which are very easily soluble in water and insoluble in ether. They have proved to be valuable -ant-isyphilitiea characterized by a mild action and as they are not irritating and not corrosive they are highly valuable for internal application especially for subcutaneous injection. They contain the mercury so firmly combined that on adding a diluted solution of caustic alkali or a cold solution of ammonium sulfid no precipitate is obtained. A solution of from 0.1-0.2 grams may be used for one subcutaneous injection. In order to illustrate my new process more fully the following examples are given, the parts being by weight:

Example 1: 3&0 parts of the oxymercuric meta-oxybenzoic acid anhydrid (obtainable by heating equimolecular quantities of mercuric oxid and meta-oxybenzoioacid with water. The yellow mercuric oxid enters into -CODNa ing formula (.IlH

l lig-O ligDKLCH-COOH [if-CONE! Other amino fatty acids 6. g. aminooxybutyric acid, amino acetic acld, serln, leucm,

sarcosin, tyrosin, etc., may be used or other oxymercuric carboxylic acids, 6. g. oXymercuric naphthol carboxylic anhydrid, having most probably the formula:

which'is obtained by heating equimolecular quantities of mercuric acetate and alphana hthol carbonic acid with glacial acetic acid and filtering olf the precipitate obtained, or oxymercu'ric salt of the sulfoanthranilic acid which can be obtained by heating acetyl-sulfo-anthranilic acid of the formula NECOCHa cum sona coon with HgO and glacial acetic acid and filtering off the precipitate, or,oxymercuric-ortho- .chlorobenzoic acid anhydrid having most probably the formula:

(which is obtained by heating together equimolecular quantities of HgO with orthochlorobenzoic acid to 130 to 140 C. After cooling the mass of the reaction is dissolved in dilute NaOH and the anhydrid is separated by introducing" 00 into the solution.)

1. The new mercury compounds of the follwing graphically represented constitution in which M' stands for a metal, X for an amino acid, and R for an aromatic nucleus unsubstituted by hydroxyl in ortho position to the -C() group, which new mercury compounds are whitish owders easily soluble in water and insolub e in ether, and con taining the mercury so firmly combined that the aqueous solutions do not give any precipitate on'the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

2. The new mercury compounds of the following graphically represented constitution following graphically represented constitusy 1 tion H omx y where M stands for a metahXfor an amino acid, and R for an aromatic'nucleus substituted by OH in meta position to the CO group, which new ,mercury com-' pounds are whitish powders easil soluble in water and insoluble in' ether an containing the mercury so firmly combined that the aqueous solutions do not give anyprecipitate' on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

4. The new mercury compounds of the following graphically represented constitution (3 x-COOM g0H,X where M-stands for a metal, and X for an amino acid, which new mercury compounds are whitish powders easily soluble in water and insoluble in ether, and containing the mercury so firmly combined that the aqueous solutions do not give any precipitate on the addition of dilute caustic soda lye or a cold solution of ammonium sulfid; and being valuable therapeutics, substantially as described.

5. The new mercury compound which has probably the formula:

and is a whitish crystalline powder easily soluble in'wnter and insoluble in alcohpl,

ether. acetnne. benzol. chlorofpgm, and con-' talus t11e-mexroury s9. firmly combmed that the aqueous solntlons do not ve an p133-v mpitnte 0n the. addition of dilute caut -lg lye or a cold solution of ammonium sulfid;

and being valuable therapeut-igs substan.

tially as described.

l test mqny whereof I have hereunt o set my hand in the presence of two subscnbxng 1O f WZHNSSQS.

n mx ENGELMANN. 1,. SJ \Vitnesses: I

CHAs. J. \Vmcnr,

WALTER VONNEGUT. 

